Water → Ethyl 3-[(furan-2-ylmethyl)(ethoxycarbonyl)amino]propanoate
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]Participants
6
Procedure
Ethyl 3-[(furan-2-ylmethyl)amino]propionate (10.8 g) prepared in the step 2 and 18.3 mL of triethylamine were dissolved in 180 mL of methylene chloride, 7.14 g of ethyl chloroformate was added by slowly dropping thereinto under cooling with ice and the mixture was stirred at room temperature for 5 hours. Water (200 mL) was added to the reaction solution and the mixture was subjected to extraction with methylene chloride. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo therefrom. The residue was purified by silica gel column chromatography to give 13.77 g of the objective compound as yellow liquid.
Workup
- temperatureunder cooling with ice
- extractionthe mixture was subjected to extraction with methylene chloride
- washThe organic layer was washed with water
- dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
- customthe solvent was evaporated in vacuo
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-630b018dd7f74135a6e4f2b3ac4b8c1a
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217031B2
Reaction notes
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